Acetic Acid → 2-Cyano-3-cyclohexylprop-2-enoic acid

HRID 225153Notes

Reaction equation

HRID 225153 reaction equation
[CH:1]1([CH:7]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([CH2:11][C:12]([O:14]CC)=[O:13])#[N:10].N1CCCCC1.C(O)(=O)C>CCCCC>[C:9]([C:11](=[CH:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:12]([OH:14])=[O:13])#[N:10]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 16275Cyclohexanecarboxaldehyde

Product 1

HCID 543858122-Cyano-3-cyclohexylprop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

A mixture of 56 g of cyclohexanecarboxaldehyde, 56.5 g of ethyl cyanoacetate, 1 g of piperidine and 100 ml of acetic acid was heated on a steam bath for 30 minutes. The acetic acid was stripped under reduced pressure. The residue was dissolved in 500 ml of pentane. The solution was extracted, successively, with water, sodium bicarbonate solution, and water. The pentane was evaporated under reduced pressure and the residue was distilled to give the ethyl ester of 2-cyano-3-cyclohexyl-2-propenoic acid (4A), bp: 120°-121° C. at 0.01 Torr.

Workup

  1. temperaturewas heated on a steam bath for 30 minutes
  2. extractionThe solution was extracted
  3. customThe pentane was evaporated under reduced pressure
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-45673c8e4ba0472793cb37168319710d
Source dataset
uspto-grants-1980_11
Patent number
US04235923

Reaction notes

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